28 Prettiest Old Fashion Haircuts That Flatter Mature Faces

Each woman shares a unique bond with her hair. However, there is a freshness and softness a woman exudes with a hairstyle that is in-tune with a particular season in her life. When I see a client studyed and finally stops resisting, takes a deep breath and genuinely says, “I am just looking for something that works with what I have” I know she is about to have one of the best experiences of her life. It is not about recreating a hairstyle from 20 years ago. It’s about honouring the best, most present version of the woman in front of us along with her features, hair, and color.

A few years back I had a client who was soft and muted with hair that had now formed into waves and was silver. She had been burnt from flat ironing her hair and she had suffered from this for years. When I finally cut into her wave pattern, we both became emotional. She stated, nearly out loud, that she had finally come to a place of recognition.

Each of the 28 Cuts I’ve added, is a tribute to a woman’s honest inner self. These hairstyles are not meant to resemble ‘old lady haircuts’. Instead, they celebrate the evolution of hair through the time it takes to grow, just as the women do. They are structured and some are loose, providing an effortless and stunning look to a grown face. Each one of these styles has that magic moment in the mirror when everything falls perfectly into place.

Photos

#1: Freshly Styled Voluminous Bob with Soft Layers

It’s easy to relax and enjoy working on this style of haircut, especially when clients have fine-textured hair and want to add the appearance of more volume. The movement and shape fine hair often lacks is provided by the layers. My favorite part of the haircut is when the ends of the hair create little waves because that helps avoid a look that is too stiff or “done.” There will be some commitment required for round brushing when blow drying the hair, but the more practice you get, the easier it will be to achieve.

#2 Chic Curly Bob with Soft Layers

If you have curly hair and are considering a shorter style, I recommend this hairstyle for you. You will love how bouncy and fun this style is. I say this because the way the layers are cut allows the curls to separate and bounce freely instead of clumping together. I suggest keeping some curl cream handy so that you can apply it to your hair while it’s damp. You might be surprised to hear that bobs like this are actually pretty low maintenance.

#3 Softly Layered Lob with a Relaxed Wave

With the combination of how effortlessly it looks and how effective it is, there’s a chance some people will consider the cut a bit lazy, but that’s a compliment. The length is also in that ideal place for a lob where it moves freely without that growing feeling. On medium to thick hair, a natural drape forms beautifully, and the gray here looks completely calculated, almost like a color decision rather than a random occurrence. If you are going to lean into the wave, I’d suggest a large barrel curling iron on low heat if you want to create a bit more wave, and I’d recommend a heat protectant if you’re going to do that a lot.

#4 Textured Soft Waves with Face-Framing Layers

This hairstyle enhances the cheekbonesand, depending on how it’s straightened, it may even take years off someone’s appearance. I believe that the overall lightness of the cut is a result of the fine hair texture working in its favor for once. The ideal hairstyle for this look is actually a lot less. Just a light hairspray will do, and then leave it as is. The texture speaks for itself!

#5 Softly Curled Bob with Warm Highlights

I like how the highlights add dimension to your hair, and the soft curls look fuller because of the highlights too. The length is perfect—not too short to seem drastic, and not long enough for fine hair to go flat. It takes about 10 minutes to achieve this look using a curling wand, and the curls will hold without getting crunchy if a little hydrating mousse is applied beforehand.

#6 Softly Textured Mid-Length Cut with Subtle Layers

I love the confidence the cut gives. Perhaps, it’s not dramatic to say there’s elegance in the way it does its job. The layers are so close to each other that you won’t notice them until the hair shifts. Then all of a sudden, this dimension shows up. This kind of layering is genius if you’re struggling with any thinning hair because it gives the illusion of more hair through movement rather than adding bulk. I like a light balayage like this one because it warms everything, and it’s perfect for people who don’t want to do an all-over color. Of course, it’s much better than being in my chair every six weeks.

#7 Layered Silver Bob with Gentle Waves

Most haircuts use layers to help create movement in the hair, rather than having the hair sit stiff like a helmet (that’s the complaint I hear most). Hairstyles with the most versatility tend to be around the shoulders. This length allows for all of the tucks and styles that longer hair won’t. This length also means you can have a sleek look with hair pushed behind the ears, and a softer look where hair can fall forward. Defined waves are also easy to maintain at this length as they do not require a big time commitment. The only tools needed are a brush and some working spray.

#8 Classic Textured Bob with Soft Jawline Framing

What makes this haircut special is the way it hits the jaw and softens everything around it. A blunt cut sits right on the jawline and can make that whole area feel pretty harsh on a more mature looking face, but the layers soften and break up that line in a really nice way. It’s the type of bob that is super sophisticated even when you haven’t done much to it, and for me, that’s the biggest compliment I can give to a haircut. It will keep its shape really well, so just make sure you get your trims every six to eight weeks.

#9 Curled Silver Bob with Easy Bounce

If someone says she wants to wash her hair, put in some product, and leave looking like she tried, this is the cut I’d give. Curls that are chin length have just enough weight to fall into place, and those silvers are really shining. A little mousse, and you’re done! I’ve given this cut to women who spend 45 minutes on their hair every day, and they can hardly believe how fast it all comes together.

#10 Softly Textured Ash Blonde Bob with Subtle Waves

The ash blonde looks great with her skin tone and cooler shades of blonde can really enhance an older face. With the right undertone, it gives an illuminative impact that warmer shades just don’t seem to achieve. The texture is soft and romantic without being too fussy. One thing to keep in mind is that ash tones do require a bit of upkeep, and a good purple shampoo will be key to controlling brassiness between appointments.

#11 Warm Copper Waves with Soft Bangs

I always get happy every time there’s a new copper hue! This one has a warm, almost autumnal richness to it which, when paired with the right tone, can be super complimentary. I’m also a big fan of the bangs, it feels like they soften the forehead just enough so that it’s not really hiding the face. The waves add a lot of movement too, which stops it from feeling too heavy. Just a heads up, red is always going to be the quickest fading color, so warm copper tones like this are going to require a color depositing conditioner to help it stay like this longer.

#12 Softly Curled Shoulder-Length Cut

What I mean is it will please a lot of people, and for good reason! It’s versatile for all types of events, whether it’s a Tuesday grocery run or a fancy dinner, and the curls keep it from ever looking boring. With this kind of haircut, and with medium density hair, you get the bounce without the struggle, which is the sweet spot. Personally, I would go for a lightweight holding spray after curling, rather than anything a lot heavier, as that would keep the curls from moving naturally throughout the day.

#13 Vintage Curled Pixie with Soft Volume

I love this kind of pixie! It takes poorly executed I-just-gave-up-on-my-hair looks and turns it into an intentional style, with tons of character. The length combined with the curls creates great volume and gives the appearance of having double the thickness to fine hair. It’s fun, but not too playful which is a hard balance to hit. A touch of texturizing paste warmed up in your fingers and scrunched into the curls is all it takes!

#14 Voluminous Curled Mid-Length with Soft Highlights

These highlights look amazing, and the way they catch the light creates a full look that the curls really amplify. The slight side part is a nice relaxed touch, and I find it much more interesting than what a center part would offer. I won’t pretend that keeping this level of curl definition takes no effort because it does, but if you find the styling process more of a chore then this look is really rewarding to live with.

#15 Textured Curly Crop with Soft Volume

If you have naturally curly hair the cut allows your hair to do what it wants to do and gives it a nice shape. The ends have been layered to remove bulk and create movement instead of a triangular silhouette, which is the ultimate struggle with a lot of curly hair. The cut also beautifully softens stronger features without downplaying them. It is a low effort haircut, but if the weather is humid, I do suggest you have some anti-frizz serum available.

#16 Classic Rounded Bob with Soft Silver Highlights

Rounded bobs are sooo satisfying. Everything about this haircut just works. The silvers and grays create dimension that is so much more interesting than just one flat color. The rounded fringe is also doing so much work and directing all the attention right to the eyes and cheekbones which is just what you want to highlight. The shape is really what makes this haircut so good so feel free to come in for trims often! Once it starts to grow out unevenly, you will seriously lose the whole effect.

#17 Soft Curly Crop with Gentle Volume

This haircut looks easy, which is proof of a good hairdresser. The curls give a lift to the whole face. This haircut works well for women with rounder faces, as it gives height without adding width. Expect to come in for a trim more often than you would with a longer haircut, about every five to six weeks. Daily styling will take very little time.

#18 Textured Curly Bob with Tonal Depth

A nice touch is the gradual shift in color along the lengths of the hair. It’s not a in-your-face color job, but those little details really contribute to the richness and dimension of the hair, almost like you have nice lighting throughout your hair. The shoulder-length curls have just enough weight to drape nicely without being completely stretched out, which is the perfect balance with curly hair, so I’m sure you will appreciate that. The layering gives the illusion of lightness, even when there is a lot of texture.

#19 Soft Curly Lob with Natural Silver

This may be my favorite in the range because it feels like an exhale. It’s not trying too hard, just sitting nicely with natural greys woven in. The waves are relaxed and loose enough to feel intentional. The length is quite forgiving – it’s long enough to pull back if you need to, but short enough to feel fresh. If your hair is fine, placing a root volumising spray before drying will keep it from falling flat by the afternoon.

#20 Silver Volume Updo with Soft Waves

There are no two ways about it, the method to execute this hair style can seem complicated and intimidating, and it can be a little overwhelming if it is your first go at it however, in the end, it does not matter what the final hair style looks like, but the instructions to execute the style. The hair style focuses on having soft strands on the sides of the face, and it also has just the right amount of volume at the crown of the head. After some practice, and a few bobby pins, you are set to achieve this style. The hair in the picture is of a good density, fine, and textured. The texture will work by providing the necessary grip to hold everything in place. Finally, use a soft and flexible hold hair spray to hold the style in place without it looking too crunchy or stiff.

#21 Chic Textured Pixie with Soft Layering

An amazing pixie cut can look really empowering and here she has had enough texturing done to the top of the hair so that it does not look too flat or too masculine. The crown layers create a bit of height and softness which makes a difference. On a practical note (which I always mention) your earrings get noticed and your neck gets accentuated which is nice. This shape really works on fine straight hair as the layers create an illusion of greater density of hair.

#22 Textured Short Bob with Soft Bangs

The blended bangs look awesome and almost look like they aren’t bangs. That chin length looks so good to elongate rounder faces. The messy, tousled look, while I am sure takes some work, looks like you ran your fingers through your hair and walked out the door, which is a good look to go for. On finer hair, a dry texture spray will give you that piece-y separation without weighing anything down.

#23 Soft Textured Gray Bob with Wispy Bangs

I believe wispy bangs really help soften the look of a fully gray bob. It adds a nice touch to the whole look. The length is nice because it makes it easy to manage. The fine texture is nice because it creates that nice feathery look at the ends. A little bit of product is all that’s needed to keep the volume from disappearing by the end of the day. Nothing too heavy. Just a bit of root lift spray when blow drying.

#24 Textured Gray Bob with Gentle Waves

The waves are so realistic that you would assume her hair was actually styled, which is an excellent compliment to the work. The ends are layered with just the right amount of softness to add some dimension to the cut, so it doesn’t appear as a solid block. The length of this grey bob is also nice because it has a lot of swing. It’s a lovely look on her and is of course completely age appropriate. It doesn’t look like it is trying to prove anything.

#25 Textured Gray Curly Bob with Lift at the Crown

The crown’s soft under layering is the magic of this entire cut, creating lift right at the top, and giving the whole shape an energy that shorter curly cuts lack. Curls can spring up most effectively at a length just above the shoulders because they won’t be weighed down. On fine to medium hair, I would prefer something that defines the curls without the crunch and I typically suggest a light weight curl gel applied to sopping wet hair and then diffused. The gray looks beautiful here, and with the curls, the texture is so full and healthy.

#26 Vintage-Inspired Curled Bob

I absolutely love the Old Hollywood look, and I think it really suits a more mature face. The chin-length curls look so polished, but they don’t look too stiff, which is a really difficult balance to achieve with vintage looks. They can easily fall into costume looks, so this is really well done. If you want to take it another step, then I would suggest a couple of softer highlights in the front pieces, which would add dimension. The curl pattern is definitely modern and loose, but it’s also got that set quality that gives it a lot of character.

#27 Lively Curly Cut with Natural Bounce

This is ideal for women who have straightened their curls for years and have made the decision to stop. When the hair is shoulder length, this look is so flattering with that kind of natural texture because the curls have plenty of space to move and separate instead of compress into one another. The coloring here shows off the curl definition so beautifully, with the lighter tones catching the ridges of each curl. If you’re embracing your natural texture, the most important thing isn’t a specific product, it’s the commitment to keeping your hair moisturized, and for that, a good deep conditioning mask once a week will make everything else easier.

#28 Softly Layered Gray Bob with Wispy Bangs

Soft layers and wispy bangs look amazing on gray hair and honestly look good on everyone! The layers shape and frame your face without hiding it, and the bangs soften the look without being an overwhelming feature. The gray is intentional and beautiful rather than a color that just happened to you. Of all the lengths we offer, my medium is the most universally manageable. It’s long enough to give you that feeling of having a good amount of hair, but not so long that you have a project to do every morning. Non negotiable regular trims every 6 weeks are essential because that is where you start to lose the shape and movement that let the cut shine. The longer you wait, the more layers you have that just grow together.